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Learn from a legend. $18.7M and 585 roofs in a single year.
Two days in Rosemont with Dan Walrack of Go Beyond the Hustle: a roofing sales rep for 27 years, a former owner, and a licensed adjuster. Day one is how to sell. Day two is how to build a sales engine that doesn’t depend on you.
Nov 30 to Dec 1, 2026 · Rosemont, near O’Hare, or live on Zoom
Dan Walrack
Go Beyond the Hustle
It’s been a great year. It isn’t here forever.
2026 brought Illinois storms nobody working today has seen, easy work, and a wave of new roofers licensed to chase it. Companies grew, new ones started, and there was room for everyone. That is the setup for 2027: more licensed competition than the state has ever had, and fewer roofs falling out of the sky. It won’t be knock on a door, hop on the roof, sign the contract.
Sales is oxygen. Take the off-season to build a process, and walk into 2027 ready for it.
Who’s this for
Sales reps who want a real career
Dan is not a coach who used to sell. He is a working rep, still on driveways every week, 27 years in. Day one is the process, the conversations and the habits he uses now, taught by the person using them.
Owners at $0-5 million
Most companies stall because the owner is the sales process. Learn a repeatable process first, then learn how to hand it to other people and scale it. That is the unlock, and it is what day two is built around.
Established companies ready for the next level
Your systems exist. The question is whether your sales team runs on one. A documented sales process is one of the first things roofing roll-ups and private equity buyers look for in an acquisition, and it pays for the two days on the first roof it sells. One key insight could mean 50+ more closed roofs next year.
This isn’t for everybody. If you’re happy where you are, jobs small and margins tight, and your sales plan is hope, this isn’t your class. If you plan to be bigger in 2027 than you were in 2026, it is.
Two days. Two jobs.
Day one: sell the roof
Mon, Nov 30- A repeatable roofing sales process. Dan’s 5 C’s, creating opportunities, and controlling your own schedule.
- The homeowner conversation. Reading the customer, building trust, scripts and frameworks that don’t sound scripted.
- Objections and follow-up. Keeping control of the opportunity after you leave the driveway.
- Retail versus insurance restoration. Insurance terminology, working professionally with adjusters, and where the two sales differ.
- Live role play and Q&A. Real contractor and homeowner scenarios, with Dan in the room.
Day two: build the engine
Tue, Dec 1- From salesperson to owner. The shift in thinking that most contractors never make.
- Hiring, culture and accountability. Building and managing a sales team that produces without you.
- A pipeline beyond the storm. Marketing, referrals, networking and community involvement that keep the phone ringing in a dry year.
- Protecting profit while growing. Time, priorities and the systems that keep margin in the business.
- A business that doesn’t rely on you. Consistency, systems, and long-term growth.
Two licenses, one opportunity only Illinois offers.
Illinois lets a roofing contractor also hold a public adjuster license. Across both days you learn how to properly pair the two: when the roofing license does the work, when the PA license does, and how to run the insurance sale so the pairing maximizes every claim.
Meet Dan Walrack.
Dan graduated college as a physical education teacher with a job lined up. A mentor talked him into chasing hail in the Twin Cities instead, and he has sold roofs every year since, 27 years and counting. He owned his own company for over a decade, sold it, and went back to what he likes: selling, on his own schedule, without an owner’s stress.
His numbers are his own and he says them out loud: 100 jobs a year is the floor he has cleared for 25 straight years. His best year was 585 roofs and $18.7 million in residential sales, by himself.
He and his wife Tiffany have been married 26 years and have four sons. The rule they built the business on is simple: be a good human.
Hear him before you meet him.
The Game Has Changed: How Winning Roofers Sell in 2026
$1M in Roofing Sales = Minimum Wage? The Brutal Truth
Why Chicago Roofing School is hosting this.
Since 2010 we have put Illinois roofing and public adjuster licenses in the hands of thousands of contractors. The question we hear the week after every class is the same: how do I grow? This is the answer, taught by someone who still does it every week, in a room full of other owners and reps.
Learn how to separate yourself from every other roofer offering a free inspection, how to use the insurance process instead of fighting it, how to build real systems instead of winging it, and how to make a real connection with the property owner. What’s your close rate? You’ll leave with a lifetime of skills, and one extra roof pays for the class many times over.
What’s included
- Two full days of instruction, 9 AM to 5 PM
- Course materials, yours to keep
- The Dan and Tiffany session at the end of day one
- Certificate of completion
Where and when
- Monday Nov 30 and Tuesday Dec 1, 2026
- 9 AM to 5 PM each day, one hour for lunch
- Rosemont, IL, near O’Hare
- In person in Rosemont, or live on Zoom.
Questions.
Is this a licensing class?
No. This is sales and business training. If you need your Illinois roofing or public adjuster license, those are separate CNTC courses, and this class is built for people who already hold one or work for a company that does.
Can I send my whole team?
Yes, and we recommend it. Owners and reps sit the same two days, so everyone leaves with the same process and the same language. Team rates apply for multiple attendees from one company. Give us a call!
Will I receive a certificate?
Every attendee leaves certified as a Certified Roofing Sales Professional. All certificates are signed off by Dan Walrack’s Go Beyond the Hustle and Chicago Roofing School, two recognized names in the Midwest’s roofing world.
Why two days?
Day one teaches the sale. Day two teaches how to build the business around it. They work together, so sales reps and owners build the systems, processes and habits that supercharge the business side by side.
Can I join remotely?
Yes, but we strongly encourage attending in person. The sales role play and the Q&A work best in the room, and you get to interact with roofing contractors who have either been in your position or are in your exact position now.
Two days. Nov 30 to Dec 1. Reserve your seat.
Call us with questions, or send in a form and we’ll walk you through enrollment and team rates.